Studies on the Periodic Acid Oxidation of N-Glycosides. VIII

Periodic Acid Oxidation of Anilines. (1)

Abstract

Periodic acid oxidation was attempted with monohaloanilines, aminophenol, anisidine, phenetidine, phenylenediamine, aminoacetanilide, aminobenzaldehyde and its oxime and phenylhydrazone, aminoacetophenone, o-nitroaniline, N-2, 3, 4, 6-tetraacetylglucosyl-p-toluidine, 2-bromo-4-methylaniline, 2, 4, 6-tribromoaniline, carbazole, benzylamine, phenylhydroxylamine, nitrosobenzene, hydrazobenzene, azobenzene, azoxybenzene, and p-nitrosodimethylaniline. Of these, phenylhydroxylamine, hydrazobenzene, and p-nitrosodimethylaniline reacted with exactly one mole of periodic acid to respectively form nitrosobenzene, azobenzene, and p-nitrodimethylaniline. Oxidation was not effected with o- and p-aminobenzaldehyde, o- and p-aminoacetophenone, o-nitroaniline, N-2, 3, 4, 6-tetraacetylglucosyl-p-toluidine, carbazole, benzylamine, nitrosobenzene, azobenzene, and azoxybenzene.